Jay Leno is a car guy’s car guy, with one of the most amazing collections of classic, contemporary, and bat-shit one-off vehicles ever assembled. He also happens to be a mensch, giving his time and money to a variety of worthy causes. This week, at the annual Pebble Beach Concours d’Elegance—the nation’s premier classic-car show and upscale-lifestyle extravaganza—he’ll be raising money for a very worthy charity by selling off a rare vehicle from his collection. (Coincidentally, George Clooney is doing something similar.)

We gave him a call to discuss his charitable endeavors, the K.G.B.’s technology gap, driving an antique wooden car that’s literally on fire, and the worst vehicle he’s ever owned. Highlights from our conversation are below.

Jay Leno: Yeah, we’re auctioning off a car as a benefit for Fisher House. It’s an organization that builds houses for veterans that have been injured, and the veterans and their families can move into the house, and stay there for as long as they want, and everything is paid for. And it’s not like government housing; these are real mansions, and they have the big 3-D flat-screen TVs, and the best linens, the best beds.

Since we’re in the war business, you know, I guess this is what happens—you have more and more of these guys and women come back in bad shape. But Fisher House takes care of them in the way you think the greatest nation on Earth should take care of someone.

And what car is it that you’re going to be auctioning off?

I have the second new Fiat 500 ever produced. The president of Fiat got the first one; I got the second one. So I’m going to auction that off up at Pebble Beach. I’ve thrown in a couple other perks—a tour of my garage, whatever it takes—as well.
I’ve been to your incredible garage. Why that car out of all your glorious cars?

If you’re going to auction off a vehicle—especially when you’re dealing with the public—it needs to be something that’s safe, something that’s fairly recent. So it’s something you can do without worrying that you’re giving someone a Model A, and if the brakes fail—well, it’s your fault.
I’m sure people ask you about your collectible cars all the time, but what about the really crappy cars you’ve owned in your lifetime? Can you tell us about some truly shitty vehicles you’ve owned?

When I first came to town, when I met my wife, I bought a Vega for $150. A horrible car. My favorite story about it is, my wife called me once, sounding panicked, and I said, “What happened?” and she said, “I went around a corner, and a piece of the car fell off.” Just a big chunk of the bumper. Clang! But I’m like Father Flanagan in Boy’s Town: There are no bad cars. There are just cars that need to be loved and taken care of.
Come on, there must be some other really bad ones in your history—you know, beloved, yet troublesome.

It depends on how you define bad. I have a Russian car called a Volga, a GAZ Volga—it’s an old K.G.B. staff car. This was built in the early 60s, at the height of the Communist era, and it is so incredibly poorly put together. It’s fascinating because you compare a mid-60s Cadillac—with a V8, and air conditioning, and power seats and all the silly things that they had—and then you look at this thing—with its 4-cylinder, essentially tractor-like engine—and it’s just amazing.
What about before you made it big? Did you ever own anything that was just humiliating to drive?

Not humiliating. I’m not the type of person who buys a car to impress people—most women are not really impressed by a guy in a 1909 White Steamcar. I do have the distinction, however, of having the oldest car stopped for speeding on the freeway. My 1906 Stanley Steamer. I got tagged at 76 miles per hour. The cop was more intrigued that it was made of wood, and it was carrying an open flame, than the idea that I was going 76. But when you go by a cop in a wooden car that’s on fire, going 76, they tend to go, “Hey, hey. What’s that?”
Is there something at Pebble that you’re really looking forward to seeing?

This year, the featured marque is Mercer, and I have a Mercer, so I’m curious to see what some of the other Mercers are like. The Mercers were built by the Roeblings, who built the Brooklyn Bridge. And it was a great car. In fact, the company was so successful that the Roeblings decided to take a cruise. Unfortunately, the ship they picked was the Titanic, and Mercer sort of went downhill after that.
Any unicorn in your dream garage that you haven’t found yet, that you’ll be seeking at Pebble or at the auctions?

No, not really. I’ve always been happy with what I have. But the hunt is fun—something sparks your interest, and it’s like, “I’m not interested in those—until I saw this one.” And then it’s like, “Oh, O.K. I need to have that.”